The Ancient Greek General Who Mastered Surprise Attacks

Few have heard of the ancient Greek general Demosthenes, whose exploits during the Peloponnesian War have largely been overshadowed by more famous figures like Pericles and Lysander.

Not to be confused with the famous orator of the same name, Demosthenes was an accomplished Athenian general who served his polis (city-state) between 426 and 413 BCE. His signature strategy was using surprise attacks to catch the enemy off guard.

Demosthenes’ military career ultimately began and ended with disaster. This may explain why he is often overlooked in the canon of great ancient Greek generals. However, throughout most of his career, Demosthenes was a pioneer of surprise attack, light infantry tactics, and unconventional thinking.

Defeat in Aetolia

Our main source on Demosthenes is Thucydides, a fellow Athenian general and the famous historian of the Peloponnesian War. Demosthenes first burst onto the scene in 426 BCE, at the head of an Athenian military expedition to Western Greece.

The campaign was initially successful. The Athenians and their allies wrestled control of most of the island of Lefkada after Demosthenes ambushed an enemy force at the town of Ellomenus. With overwhelming numbers, the capital of Lefkada was ripe for a siege and eventual capture.

However, the Messenians, an ally of the Athenians, persuaded Demosthenes to divert his attention and invade Aetolia on the Western Greek mainland. This angered the Acarnanians—also Athenian allies—who had urged Demosthenes to maintain operations in Lefkada.

In their anger, the Acarnanians refused to assist Demosthenes. This was a major problem because he relied on their local expertise for intelligence and their capabilities as light infantry. Demosthenes sought to replace the Acarnanians with the Locrians, but he again followed the advice of the Messenians and pressed on into Aetolia without waiting for them.

This proved disastrous. Without the local knowledge of either the Locrians or Acarnanians, the Athenians and their allies entered Aetolia essentially blind. Demosthenes was surprised by the Aetolians in Aegitium who had assembled an army.

The Aetolian javelin throwers peppered the Athenians and their allies at long range and quickly retreated before they could be engaged in melee. Demosthenes’ army held until the captain of his archers was killed and he lost his ability to shoot back at the Aetolians. Demosthenes’ heavily armored hoplites had no hope of outrunning the lightly armed Aetolian infantry and were continually struck by missiles until the entire Athenian army broke and fled the battlefield.

Victory from the jaws of defeat

Demosthenes feared to return to Athens after his defeat and did not accompany the survivors upon their return. For an ancient Greek general, returning home after a defeat could be just as dangerous as the risks endured on the battlefield. He instead stayed in western Greece, awaiting an opportunity to reverse his fortunes.

The defeat in Aetolia emboldened Athens’ enemies and the Ambraciots – a western Greek people originally from Corinth  – invited the Spartans to assist their upcoming military campaign. The Spartans responded by dispatching General Eurylochus to the region as the head of an army mostly comprised of Peloponnesians.

The Spartans and Ambraciots captured several settlements before combining their forces to threaten Naupactus, a strategically vital port for the Athenians. Demosthenes narrowly avoided disaster by reinforcing Naupactus with about 1,000 hoplites. The port city had strong walls and the attackers could not conduct a successful assault if the walls were adequately manned.

The siege was abandoned but the Spartan threat remained in the region. Eurylochus and his Ambraciot allies next set their sights on the city of Amphilochian Argos. The Amphilocians and Acarnanians again turned to Demosthenes to command their forces and prevent disaster, despite his earlier failure in Aetolia.

Demosthenes was outnumbered in the ensuing battle at Olpae. However, he positioned a force of 400 hoplites and light infantry in a concealed position before the battle started. When the two armies met, Eurylochus gained the upper hand and was well-positioned to outflank Demosthenes on the left. At this moment, the ambushing force emerged and outflanked the Spartans and their allies. Eurylochus was killed in the fighting and his army fled.

The following day, Demosthenes won another victory against an Ambraciot army on their way to reinforce their companions. Demosthenes’ forces snuck out at night to occupy the largest of two hills at Idomene. They then descended on the unsuspecting Ambraciots and utterly destroyed them in a surprise attack.

Having won two major victories, Demosthenes could now return to Athens where he awaited a hero’s welcome.

Pylos and Sphacteria

The following year, Demosthenes played a critical role in the battles of Pylos and Sphacteria, two engagements that marked a turning point in the conflict between Athens and Sparta.

The campaign began when Demosthenes, on an expedition to Corcyra, decided to fortify Pylos, a strategic location on the southwestern coast of the Peloponnese. Pylos’ natural defenses and proximity to Sparta made it an ideal base for Athenian operations. Despite the initial reluctance of the other generals on the expedition who held senior command, Demosthenes convinced them to support his plan, setting the stage for a confrontation with Spartan forces.

The Spartans quickly recognized the threat posed by the Athenian occupation of Pylos. They launched a large-scale offensive, aiming to dislodge the Athenians. Demosthenes, however, skillfully used the rugged terrain and limited resources at his disposal to repel multiple Spartan assaults. His strategic use of light troops and the terrain’s natural advantages allowed him to hold out against a superior Spartan force, exemplifying Athenian resilience and tactical ingenuity.

Notably, the Spartan commander Brasidas – another rising star of the Peloponnesian War – attempted a seaborne assault on the shore of Pylos. He crashed his ship into the rocky shore and tried to rush the Athenians. However, he was struck by several missiles and gravely wounded.

As the siege at Pylos unfolded, the Spartans stationed a garrison of 420 hoplites, including 120 elite Spartiates, on the nearby island of Sphacteria to secure the harbor and prevent a complete blockade. However, the Athenians used their naval superiority to cut off supplies to the island, trapping the Spartan garrison. The situation devolved into a prolonged stalemate, with Athens unable to force a decisive victory and Sparta unwilling to concede.

To break the deadlock, Demosthenes and Cleon, an Athenian politician, launched a bold assault on Sphacteria. The Athenians employed light-armed troops, such as archers and javelin-throwers, to harass and weaken the heavily armored Spartan hoplites.

This strategy, combined with the Spartans’ exhaustion and dwindling supplies, forced the defenders into a desperate retreat. Facing starvation and relentless attacks, the Spartans ultimately surrendered an unprecedented event that shocked the Greek world and undermined the reputation of Spartan invincibility.

The surrender of the Spartan garrison, including elite Spartiates, was a psychological and strategic blow to Sparta. It marked one of the rare occasions in Spartan history when their warriors capitulated rather than fight to the death. For Athens, the victory at Sphacteria was a significant triumph, boosting morale and providing leverage in future negotiations with Sparta. The captured Spartans became valuable bargaining tools, further enhancing Athenian influence during the war.

Downfall and death

In 424 BCE, Demosthenes and Hippocrates (of no relation to the famous physician) launched an effort to seize Megara but were thwarted by the Spartan general Brasidas. The Athenians managed to capture the port of Nisaea but Brasidas’ intervention prevented the city itself from falling. The standoff at Megara essentially ended in a stalemate.

Following this setback, Demosthenes travelled to Boeotia, where he supported a democratic revolution and worked to assemble forces for a planned invasion of the region. However, a lack of coordination between Demosthenes and Hippocrates undermined their efforts, culminating in Hippocrates’ defeat at the Battle of Delium and Demosthenes was forced to abandon the venture.

Following the failure of the campaign in Boeotia, Demosthenes was sidelined for several years until he was dispatched in 413 BCE to Sicily as part of Athens’ efforts to bolster its faltering expedition against Syracuse during the Peloponnesian War.

Arriving with reinforcements, he sought to act decisively and break the stalemate. Demosthenes launched a bold night assault on the fortified heights of Epipolae, aiming to surprise the Syracusans and gain a critical advantage. However, the attack ended in disaster as the Athenians became disoriented in the dark, and their forces were routed by the combined Syracusan and Spartan defenders, led by Gylippus.

Following this failure, Demosthenes advocated for a strategic retreat, recognizing the expedition’s diminishing chances of success. However, his suggestion was overruled by Nicias, the senior commander, who insisted on continuing the campaign. When the Athenians finally attempted to withdraw, their efforts were thwarted by a Syracusan blockade and pursuit. Demosthenes and his forces were surrounded and captured, leading to his execution alongside Nicias.

Where does Demosthenes rank amongst other ancient Greek generals?

Regarding Demosthenes, historian Graham Wylie notes, “Tricks and deceit were his very stock in trade, and he used whatever weapons and troops could do the job best.” At a time when most Greek generals favored the use of heavily armed hoplites in conventional battles, his use of surprise tactics and light infantry was truly innovative.

Demosthenes’ imperfect battlefield record prevents him from ranking among the very top ancient Greek generals, like Alexander, Philip, Philopoemen, and Epaminondas. Nevertheless, he deserves tremendous credit for handing Sparta some of the most shocking defeats at Pylos and Sphacteria.